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Record Information
Version	2.0
Creation Date	2015-09-08 17:49:57 -0600
Update Date	2016-09-13 16:35:43 -0600
Secondary Accession Numbers	ECMDB24184
Identification
Name:	2,3-Dihydroxybenzoic acid
Description	2-pyrocatechuic acid, also known as 2,3-Dihydroxybenzoic acid, is a member of the chemical class known as Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. 2,3-Dihydroxybenzoic acid is a colorless solid that occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsitripeptide of serine. (Wikipedia) In E. coli K-12, 2-pyrocatechuic acid is involved in biosynthesis of siderophore group nonribosomal peptides. (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa5aff00> Close
Synonyms:	2,3-Dihydroxybenzoate
Chemical Formula:
Weight:	Average: Not Available Monoisotopic: Not Available
InChI Key:	Not Available
InChI:	Not Available
CAS number:	Not Available
IUPAC Name:	2-carboxy-6-hydroxybenzen-1-olate
Traditional IUPAC Name:	2-carboxy-6-hydroxybenzenolate
SMILES:	Not Available
Chemical Taxonomy
Description	belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
Kingdom	Organic compounds
Super Class	Benzenoids
Class	Benzene and substituted derivatives
Sub Class	Benzoic acids and derivatives
Direct Parent	Hydroxybenzoic acid derivatives
Alternative Parents	Benzoic acids Benzoyl derivatives Phenoxides 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Monocarboxylic acids and derivatives Carboxylic acids Organooxygen compounds Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Hydroxybenzoic acid Benzoic acid Benzoyl 1-hydroxy-4-unsubstituted benzenoid 1-hydroxy-2-unsubstituted benzenoid Phenol Phenoxide Vinylogous acid Carboxylic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Hydrocarbon derivative Organic oxygen compound Organic oxide Organooxygen compound Organic anion Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	dihydroxybenzoate (CHEBI:36654 ) a catechol (2-3-DIHYDROXYBENZOATE ) an aromatic carboxylate (2-3-DIHYDROXYBENZOATE )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 29.1 g/L ALOGPS logP 0.53 ALOGPS logP 1.67 ChemAxon logS -0.77 ALOGPS pKa (Strongest Acidic) 2.56 ChemAxon pKa (Strongest Basic) -6.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 80.59 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 47.83 m³·mol⁻¹ ChemAxon Polarizability 13.39 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2,3-Dihydroxybenzoic acid + NADH + Hydrogen ion 6 Adenosine triphosphate + 3 L-Serine + 3 2,3-Dihydroxybenzoic acid + 3 L-Serine >6 Adenosine monophosphate + enterobactin +6 Pyrophosphate +3 Hydrogen ion Adenosine triphosphate + 2,3-Dihydroxybenzoic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid Adenosine triphosphate + 2,3-Dihydroxybenzoic acid <> (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate 2,3-Dihydroxybenzoic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate
SMPDB Pathways:	Biosynthesis of siderophore group nonribosomal peptides PW000760 Enterobactin Biosynthesis PW002048
KEGG Pathways:	Biosynthesis of siderophore group nonribosomal peptides ec01053
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Not Available
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 36654 HMDB ID Not Available Pubchem Compound ID 6950143 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID 2,3-Dihydroxybenzoic acid BioCyc ID Not Available

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